My fiancè Jamie and her little sister Madeline have the same Jewish genes and good girl charm, but they certainly have different body types. Madeline is a taller 19 year old with DDs and a voluptuous figure. Jamie has been training for the Chicago Marathon, so her ass keeps getting smaller and more firm. Her medium perky Cs compliment the small ass quite nicely.
This past weekend the family gathered at their parent's house in Maine for some birthday celebrations. Dinner followed by board games led to a very PG-13 version of 'Never Have I Ever.' As the parents and older folks made their way home and to bed the game continued with more raunchy questions.
Maddie was wearing blue and white checkered pajama bottoms and I noticed about halfway through the game that her teal thong with pink ribbons on it was hanging out. She must have caught me looking because she pulled it out of sight and looked right at me with a wink. Holy shit.
As if to play off of my perverted peeking, she started asking about the fact that I must not have been with any girls other than Jamie. Slightly inappropriate considering the younger cousins were still sitting within earshot. The math was easy in her mind, as Jamie and I had come to age together for over 10 years and were indeed exclusive partners.
My awkward way of answering the question must have sent the wrong (or right) message because Jamie ended the game and announced that she was going to bed.
Madeline and I both agreed that we weren't tired and she suggested that we grab a beer and get in the hot tub. I had no idea where this was going. I changed and met her out back in the tub with a few Lagunitas IPAs.
To my surprise she emerged from the house and into the gazebo/tub wearing nothing but a sports bra and the the same teal thong.
"I saw you peeking at my ass so hopefully you can handle yourself, I left my bikinis at the Cape Cod house last weekend."
Maddie must have found the water too hot because she couldn't seem to submerge her whole body gracefully. Watching her attempt to lower and re-lower her bottom half in the hot water was way too sexy. I was already hard as diamonds from seeing her cute little ass bounce in and out of the water as she struggled to adjust.
Hoping that everything was back to normal, I sipped my beer and tried to make small talk about Lagunitas opening up a brewery in Chicago. She bitched about the strong flavor and asked if I had anything else. I was staring at her wet, now see through white sports bra and completely tuned out.
Here I am caught red handed for the second time gawking at my future sister in law. She jumped across the 8 person tub onto my lap and said I needed to keep my eyes off her body while laughing and putting her hand on my chest. There was a silent pause when I felt her run her hand from my collar to my waistline.
Maddie looked me in the eye and said I must be lying about only fucking one girl. Insisting that I have been loyal to Jamie must have turned her on even more.
Maddie lifted her ass out of the water again, turned around and grabbed a beer. Confused, I asked why she wanted another, seeing as she just finished complaining about the flavor. "It's not for me, I have to get you drunk so we can keep having fun out here."
Madeline bent over the tub to grab my beer key, while "accidentally" putting her beautiful curvy backside right in my direction. I could see the side of her pussy was coming out of the little teal number and I audibly let out a little wimper. I. could. not. take. it.
"Madeline you know I'll never cheat on Jamie right?" I could see the now-obvious sexual energy radiating from her.
She turned around and looked at me confused. Returning to my corner, this time she sat on my lap facing toward me with both legs spread on each side of my now throbbing crotch.
"Um, what is happening?" I poorly faked innocence.
With that she reached behind her back and pulled the bra half off letting her nipples show, which broke the camel's back. I grabbed the bra and ripped it over her head, not wanting to wait another second.
"I can't fuck you Maddie."
"Shut up," she whispered.
We made out with our bodies half in the water for the next few minutes, she was grinding on my now untied trunks under the water. I could see the thong beginning to slip off and reveal her shaved cunt.
With her tits exposed she hopped out of the water unexpectedly and suddenly. Grabbing my hand the whole time, she whispered "I wanna take you to my bedroom." We ran through the patio doors, across the living room and up to her bedroom with her ass and tits completely exposed. Thank god no one was awake.
On the way upstairs I could not help but look at all of the photos and decorations that reminded me of Jamie. Here I was hooking up with her little sister just 20 feet down the hall from where she is sleeping in her room.
Maddie pushed me into her desk chair so I sat down unsure what to expect. She bent over in front of me, shaking her perfect ass and pussy at my face. She was obviously freshly shaven and still dripping water from the hot tub. I decided to fingered her while she bent over and buried her face into the floor, her soft moans and heavy breathing were risky and made me nervous. Jamie or their parents could easily hear if awake.
Without warning her I took my dick out and pressed it against her little slit. She turned around and scolded me. "Were taking this slow! Does Jamie even know how to edge you?"
Maddie stood up, grabbed her pink Victorias Secret bathrobe off the back of her door to cover up and motioned toward the bed. She laid down next to me, but not before grabbing a jar of Coconut Oil from her nighstand.
"I'm going to make you squirm and beg to cum, lie back."
Maddie was stroking my cock slowly with just two fingers for at least 5 minutes. The melting oil on her hands made for the silkiest skin on skin contact you can imagine. I felt like I was going to cum, but that's when she stopped in her tracks, slipped the robe off to reveal her nipples.
"I need to cum all over you." I begged.
"Not until I let you, I'm going to make you scream."
Maddie repositioned herself in the reverse cowgirl position with the robe still 2/3 on her. Her ass was peaking out of the short robe. She turned around and stroked me slowly with her, tiny wet hands. I didn't notice at first but she was fingering herself while touching me.
Maddie stood up and dropped the robe, now only donning the teal thong that was now visibly wet. I stood up to meet her but she shoved me back down on the bed.
Her next move was to bend over and touch her ankles. Her pussy was clearly visible through the thin teal satin, it was driving me mad. I began to stroke myself, which she could hear. This prompted her to bounce on top of me and stop my motion.
She reached to her nightstand and grabbed two items. One was a pink rabbit vibrator, which she placed in my hand. This was getting more insane by the minute. The other item was a lamb skin condom, (which is a bit of foreshadowing).
Assuming the reverse cowgirl position again, she dropped the thong below her pussy this time. I turned the vibrator on and to her surprise shoved it into her her tiny pink ass.
"Aww, fuck that was not-" she barely managed to say before I began to aggressively finger bang her beautiful white, smooth and now oily slit.
Burying her face in the down comforter I could almost hear her screams of ecstasy. Thank god she knew how to mute herself.
Maddie flipped around with the rabbit still vibrating in her ass, and kissed me with force equivalent to hurricane Katrina. She took the opportunity whisper something I'll never forget.
"I'm a virgin, please don't be mad." 10 or 15 seconds passed as I took this in.
"My sister said her first time with you was perfect, I can't trust anyone else to fuck me. I’m only 19, I don’t know any mature guys like you."
I sat in silence and dropped my hands to my side, all I could hear was the vibrator (still in her ass, comically). Rolling her over forcibly, I said “OK, but this is seriously unforgivable, one time only and we can’t tell anyone.” She grinned and reached under herself to pull the battery charged rabbit out of her ass.
I pulled my boxers off and reached for the jar of coconut oil to re-lube myself, albeit unnecessary, she was totally wet. I set my oily cock on her stomach as if to say ‘your move.’
Maddie rubbed my member on her cheek while looking up at me and laughing with excitement. “I remember the night Jamie lost it to you, I was only 15 but she told me the whole story when she got home.” Maddie had been jealous of her older sister for nearly 4 years, my mind was blown. I guess she idolized her sister to the point that she wanted to lose it to the same guy as her. I was taking advantage.
Maddie was lightly stroking my cock with her lips while I let my fingers graze the outside of her pussy. This went on for more than 10 minutes, driving me absolutely mad. I kept trying to reposition her for the final act, but she was resisting.
Finally we rolled over and I put my dick right in front of her slit and made eye contact, “This is it, are you sure?”
Fucking her was the greatest feeling since I took Jamie’s virginity nearly 5 years ago. I took it as deep as I could (bareback) without causing pain, because she was clearly wincing and trying to stay confident. I was too turned on by her painful gestures, so I kept fucking her harder. It looked like she was about to cry with ecstasy. Unfortunately I could not last much longer.
The teal thong was now around one of her ankles, so I grabbed it and held it to my face. The smell of her pussy was exactly the same as Jamie’s, how much different could it be? Although inexperienced, Maddie had clearly planned for this. She flipped over and laid on her stomach, while spreading her legs to reveal the most breathtaking angle I had seen of her young body. I reinserted myself and went at it even harder, now she was really in pain. This new angle gave me clearance to fuck her even deeper than before.
I reached around to grab her tits, and noticed that she was clearly crying. There was no question that she was serious about being a virgin. Although I felt somewhat empathetic, this turned me on way too much. Still fucking her unprotected, she suddenly realized the risk she was running.
“Shit I’m not on birth control, pull out! pull out!” Now the condom-grab made sense.
I was clearly about to come, pulsing and struggling to continue fucking her. I pulled out and shot several warm ropes all over her perfectly positioned ass. Now realizing what had happened, I backed off, still with the thong in my hand. She laid motionless still whimpering and catching her breath. I don't think she came all the way, honestly.
I stood up and took it all in, there she was, the teenage little sister of my fiancé. Having just taken her virginity, I felt a little remorse, especially after I noticed the small amount of blood dripping from her vagina. She was clearly embarrassed and somewhat delirious. Madeline immediately collected her robe and covered herself.
Looking at the floor at first, she looked up at me, moved toward me and kissed me again on the forehead. She bit my ear and said “Thank you times a million, I’ll never forget this, but you can’t tell ANYONE.” I looked down and saw more blood running down her leg.
I left the room, showered off and met Jamie in bed. She assumed that we had passed out on the couch downstairs, not suspecting a thing. I kept the teal thong as a souvenir, and being my perverted self I have vacu-sealed it for later enjoyment ;-)
Source: reddit.com/r/gonewildstories/comments/3qt16b/i_took_my_fiancés_little_sisters_virginity_first
Since the weekend, how have things been between you and Madeline? Do you really think this will be a once off thing? Are you hoping for more?
I can’t stop thinking about her, we’ve been texting about her visiting Chicago. Although when she visits Jamie will be here… Trying to get her to send me n00ds….
Have to ask… is Madeline brunette or blonde?
Brunette!
How are you going to manage this?! What did she think about giving you get virginity? Happy, satisfied? It totally sounds like an ongoing thing. Good luck, if you get the pictures, try taking a video after that!
sister sex is always fun
for the love of all things holy, please share
> hard as diamonds Autist detected.
yeah, you’re definitely gonna get caught unless you stop and also ditch the thong.
I was going to ask about guilt, but this comment answers my question.
If you get any of those pictures can you send them my way? You plan on continuing to fuck both of hem even though if you get found out it will likely fuck so much shit up.
You’re going to lose Jamie. Sooner or later. It will happen and it will be incredibly painful because all three relationships will be broken. Even if you end it now, you’ll always have fucked your wife’s little sister.
You lucky fucker
Hid the thong in my Nintendo 64 box, Jamie isn’t going in there.
Thx for the advice, I’m going to come clean before the wedding if Maddie allows it.
Looks like we share a birth year!
It was indeed fun.
Very guilty indeed, she was so paranoid that she went to the gyno on Monday to ask about the bleeding. Due to no contraception, they asked her to come back for a pregnancy test. Yikes!
How will I manage? By trying to tell Jamie in the most graceful way possible. Honestly I don’t think Maddie orgasmed from our sex, just from being fingered. Maddie went to the gyno to ask about the bleeding, she was terrified when they asked her to take a pregnancy test (no contraception.) Apparently she was prescribed the BC pill but hasn’t been taking it. Fuck..
:D Have you gone bareback with your fiancee before? Wish mine had a teen sister…
Might be better to just confront it now and get it over with now. Will blow up worse later especially if you keep fucking them both.
Jamie and I are exclusively bareback, even when we fucked as 15/16 year olds it was bareback. She has always been on the pill, and now the IUD. Let me take a moment to recommend the copper non hormonal IUD, does wonders for increasing sex drive.
Thats a good point, I hate to say it but fucking her twice is just as bad as once. Will probably make sure it happens one more time before coming clean. That’s what Madeline and I have been discussing via text today.
Unfortunately I don’t think she’s going to send pics. Might let me take them tho.
This is sad. I feel bad for your future wife.
Then there is a till hope!
?
The fuck? If this story is real, never tell her. If you want to break up, then do it. It will fuck their relationship forever. It’s better left unsaid.
Looks like her and I are going to fuck one more time then make a decision when we can chat in person. She does NOT want to tell Jamie and I’m a bit torn.
That’s down right cold dude.
Karma comes back around ;) maybe next time you should think with your brain not your dick.
You don’t deserve either woman.
Has copper had any downsides that you know of? My fiancee is going to get on IUD and we were thinking the hormonal possibly. Can you elaborate on the difference in your opinion?
I could not agree more, but I love the saying "Better than I deserve." Sounds douchey, but it is worthwhile to take what you can, live fast and leave a sexy corpse. Only young once.
Well, if you get the hormonal IUD it has the same side effects as some forms of the pill. Such as: weight gain, lack of sex drive and hardcore emotions/anxiety. If your girl doesn’t mind the hormones go for the hormonal. If you want to ease the side effects go for copper.
That’s why you shouldn’t be putting your fiance through that and get a girl that would swing with you.
Will be a lot of one last times or sneaking around at family gatherings. You will get caught, the time is now to come clean. This sure got serious but seems like people want to help you make better decisions.
damn bro, you fucked up so hard you don’t even realize it. Good luck
Look guys, the point of /r/gonewildstories is to read sexy stories. If you find certain things unsexy, that’s fine. But if you’re having a moral quandary about OP’s circumstance, keep it to yourself. I’m sure he’s torn between the great feelings that he had with his fiance’s sister and the feeling of guilt that comes with it; we don’t need to have people saying "You’re an asshole" or "You fucked up" or the linguistic equivalency of "I’m a better person than OP for not doing that," because it’s just heaping more shame on him. It’s juvenile, and certainly not what GWS is about. So stop commenting like that, and stop downvoting all of OP’s comments just because he doesn’t live up to your moral code. EDIT: Especially when he wasn’t asking anybody for advice.
Dude…fucking her once is heat of the moment and you can tell Jamie it won’t happen again. Fucking her twice is deciding to do it and making it happen, even though you’re engaged to her sister. Lot harder to explain than a heat of the moment thing. Do what you want, but don’t kid yourself, huh?
Why the hell are you marrying this woman? You can’t even keep it in your pants now, what do you possibly think will happen after you marry her? You clearly don’t respect your relationship with her or her relationship with her sister. Get out of there and let the poor girl put her life back together.
Hey I appreciate it! Don’t mind getting downvoted, that’s kind of the point of Reddit. Sometimes you get upvoted & sometimes you get downvoted. I wasn’t asking for advice, but I like the dynamic feed of thinkers to put whatever they want in the comment section of all threads including mine.
While I agree with you, the plan is more dynamic than you might think. I should have shared these details above. Jamie has one "hall pass" from me to use before the wedding in December. She has been pretty forward about her plans to fuck a certain soldier in Israel next month. The guy is technically her second cousin (is that weird or common in Israel?). I was supposed to have a "hall pass" too, because we thought of the idea as a mutually beneficial thing. I will be telling Jamie that I’ll use my hall pass on her sister. Hence fucking her one more time.
Jamie and I did actually agree to give eachother one "hall pass" before the end of the year.
This is what I’m worried about….
Well honestly, she will never forgive you, or her sister. She won’t ever trust you again , and will be scared to trust anyone else again. If you truly care about her, leave her. It’s not fair to put anyone through such a situation
Yeah, well I’m sure she didn’t think you were gonna use that to fuck her little sister.
lol did you not even see the movie hall pass? no one who fucks is happy! the movie was about how hall passes are a bad idea
Telling her is selfish. Carry the burden you created and don’t do it again.
Lucky bastard. That sensation is out of this world with my ex. Fiancee refuses to even consider it
Never tell. I don’t give a fuck about the hall pass. Of course you are texting and going to do it again, it’s forbidden and therefore super extra hot. Don’t tell. It will never be forgotten and will just cause pain.
How is it selfish? It makes me an honest man and makes it harder on me.?
It is indeed extra super hot, I have fapped to her fully clothed facebook pics several times today ?
But is it that crazy to do it just one more time? Madeline already says shes going to tell Jamie if I don’t eat her out when she visits Chicago. Jamie will be in class and out running for hours giving us plenty of time.
Honestly I don’t know how lucky I am. It was in the back of my mind as soon as Maddie came out of the house in the thong. The hall passes were here idea…
I agree it is pretty short sighted, but wouldn’t it be hard for anyone to resist?
While I agree that this is right time to come clean, that would be the conservative play. I’ve already opted not to take the high road, right? So I figure if we have one more encounter, that will satisfy me enough to quit. Her claim is that we need more time for proper foreplay and edging. We both think we rushed it and would have rather waited to fuck. She claims she knew she was going to fuck me for the last 2 years. Honestly, I didn’t see it coming. Though I do remember staring at her a lot on the beach in Costa Rica two years ago when we were on family vaca.
Trust me above all I’m guilty, secondly I’m incredibly lustful.
I mentioned this above, but she has been very forward about using this hall pass to fuck her distant cousin in Israel. She asked me if she needed to use protection with him ?. Likely that he gets to cum in her.?
Would it be hard to resist fucking my fiance’s little sister? I would say most people would agree that it’s pretty easy to resist that.
I give up -.-
Jesus dude, stop while your ahead!
Maybe you just don’t need to be in such a committed relationship if your lust can’t be satisfied by one person. Or maybe Jamie would consider an open relationship (although not with her sister I’m sure). Or maybe you actually can get all you need from Jamie. Is this the first time you’ve been with someone other than her?
You know the saying: "When the stakes are high, up the ante." In OP’s case, he can up the ante and try for a threesome.
Not going to lie, that is the ultimate fantasy. Though, imagining the two of them naked side by side is pretty unrealistic.
Yes this was my first time with another girl, hadn’t even made out with another girl before Maddie.
#realitycheck
How is it selfish? Telling her makes it incredibly hard on me, and I would accept the challenge of taking responsibility. Honestly due to the fact that she gave me a "hall pass" I can’t imagine it being too devastating.
Why the downvote on the hair color lol?
Oh trust me I realize the gravity of the situation, but honestly isn’t that what makes it so hot?
LOL BTard?
Never forgive her sister? I find that hard to believe. Madeline has been a great sister, this is probably her only lapse in judgement if you can call it that.
Not looking to swing, just looking to stay with Jamie and have a little bit of fun before we settle down.
Say what you will to make yourself feel better ;)
Note for all girls with a sister… Check your partners n64 box. For a second i thought you opened up your n64 and hid it in the internals. Now *that* would have been dedication
So instead of maybe using that "hall pass" to make it that you didn’t cheat on your partner, you’d rather cheat on her then get another go?
i live in chicago.. just sayin
So how did Halloween go??? Can’t wait for the update!
We snuck in some dancing and making out. At one point I made out with Jamie then 10 minutes later was kissing Madeline. If we hook up again for real it will be today/tonight…
no pics
Keep us posted.
Yo yo! Let’s eat at Bongo Room.
Well??? Did it happen? Also my 2 cents.. I started out just as you. The list for other women never dies. Married a couple years now and though I love my wife, I wish I had been more up front about desiring other partners regardless of the outcome of our relationship. Now I’m condemned to live vicariously through stories such as these to keep from cheating. Considering SHE bright up the hall pass, you have a serious advantage over most getting her to understand. Definitely last it all out ASAP.. As delicately as possible of course. But you got to be down with her taking other cocks too, of course
You are a terrible person. You were her first and you didn’t even get her off. Shame on you!
Okay, that was hot as fuck. Wrong or not, my pussy is wet from reading it. How did the Halloween visit go after the dancing and kissing?